The Eastern 248 Islander 2013 is a modified-V design and the Eastern 27 Lobsterfisherman 2011 is a deep-V design, so you're likely deciding between two noticeably different on-water experiences. Hull type shapes everything from ride quality and fuel burn to dock handling and resale trajectory.
On paper these two are close siblings in the size department - Eastern 248 Islander 2013 at 24,0 ft versus Eastern 27 Lobsterfisherman 2011 at 26,3 ft. Weight tells a clearer story for trailering families: the Eastern 27 Lobsterfisherman 2011 tips the scales at 4 900 lbs - 1 400 lbs less than the Eastern 248 Islander 2013 at 3 500 lbs. That difference is meaningful if you're working within a half-ton or three-quarter-ton truck's tow rating, especially once you factor in a motor, gear, and fuel.
The power gap is worth calling out. Rated to 225 hp, the Eastern 27 Lobsterfisherman 2011 has a 75-hp advantage over the Eastern 248 Islander 2013's 150-hp ceiling - enough to notice on acceleration and at cruising speed, particularly with a full passenger load.
For family outings this is probably the sharpest distinction between the two. The Eastern 27 Lobsterfisherman 2011 is rated for 8 passengers, while the Eastern 248 Islander 2013 caps at 7. If you're regularly pulling extended family or a group of friends onto the water, the extra seats on the Eastern 27 Lobsterfisherman 2011 could be the deciding factor.
Bottom line: Choose the Eastern 27 Lobsterfisherman 2011 if your priority is putting more people on the water - it handles 8 passengers and at 26,3 ft it has the deck room to back that rating up comfortably. The Eastern 248 Islander 2013 is the smarter pick if you want a lighter, easier-to-trailer boat rated for 7 that costs less to run day-to-day.